This article is part of our Tennis Picks series.
Quarterfinal play begins at Wimbledon on Tuesday, with the top half of the men's draw and bottom half of the women's draw set to take the court at the All England Club. Don't be too quick to pencil in Jannik Sinner and Carlos Alcaraz for another Grand Slam semifinal showdown, as a player who has had decent head-to-head success against one of them could put forth a spirited upset bid Tuesday. A women's tournament that has been wild so far could see another surprise result, while one of this year's top performers will look to capitalize on her opportunity after a lucky break allowed her to stay in the tournament.
All Tennis Odds & Lines are taken from DraftKings Sportsbook, but you can sometimes find more favorable odds on some of these matches by checking mobile sportsbooks such as FanDuel Sportsbook, BetMGM, Caesars Sportsbook, or any of the other best sports betting sites. We offer exclusive sign-up bonuses for some of those sportsbooks in states where sports betting has gone live.
All men's singles matches at Grand Slams such as Wimbledon are best of five sets, while women's singles matches are best of three sets. A mix of players' previous grass court results, recent form and stylistic matchups can help pinpoint intriguing betting opportunities, both among favorites likely to cruise to victory and underdogs ready to pull off upsets. The aforementioned underdogs are highlighted in the Upset Alert section, the Lock It In section covers players who can safely be viewed as overwhelming favorites, while the Value Bets section recommends enticing options in matchups that are considered closer to toss-ups.
Wimbledon Picks: Upset Alert
Lulu Sun (+220) vs. Donna Vekic
This battle between unseeded opponents is a golden opportunity for both players to reach their first career Grand Slam semifinal. Sun has thrived as an underdog all tournament and already has seven wins under her belt here, having first won three matches in qualfiying just to reach the main draw. She took out No. 8 seed Qinwen Zheng in the first round and didn't let a hostile crowd faze her in a 6-2, 5-7, 6-2 fourth-round win over local favorite Emma Raducanu. Vekic has superior power off the ground but is 0-2 in her career in Grand Slam quarterfinals and will be feeling the pressure as the favorite in this match against an opponent ranked 86 spots below her. The 23-year-old Sun had played just one Grand Slam main draw match prior to this tournament, so the lefty's playing with house money here.
Tommy Paul (+280) vs. Carlos Alcaraz
Paul has a smaller probability of pulling off the upset than Sun does in her match, but these odds are selling the American's chances short. Alcaraz has struggled to maintain his level in this tournament, getting pushed to five sets by Frances Tiafoe in the third round and losing the third set 6-1 to Ugo Humbert in the Round of 16 before righting the ship. Paul has the game to make the Spaniard pay for his lapses, as the No. 12 seed has been in exceptional grass-court form this year and is riding a nine-match winning streak that includes six wins over players currently ranked in the top 30. Alcaraz has had trouble against Paul before, as their head-to-head is tied 2-2, with all four matches coming within the last two years. Paul's excellent returning can keep him in a lot of Alcaraz's service games, so the No. 12 seed has a real opportunity to knock off the defending champion if Paul can take care of his own serve.
Wimbledon Odds: Lock It In
Jannik Sinner (-450) vs. Daniil Medvedev
Medvedev has benefited from a favorable draw for a second consecutive Wimbledon, but he still isn't all that comfortable on grass. He reached the semifinals here last year without facing a seeded opponent, then lost to the top-seeded Alcaraz in straight sets. A similar fate likely awaits the fifth-seeded Russian against the No. 1 seed in the quarterfinals this year after Medvedev beat three unseeded opponents, then benefited from Grigor Dimitrov's first-set retirement in the Round of 16. Sinner's a perfect 9-0 on grass in 2024 and has gotten better with every match here. He's coming off a straight-sets win over big-serving American Ben Shelton, and the Italian should have a far easier time against Medvedev on this surface than Sinner did in his five-set win over Medvedev in the Australian Open final.
Wimbledon Predictions: Value Bets
Jasmine Paolini (+135) vs. Emma Navarro
Paolini's a nice value as the slight underdog considering she's ranked 10 spots above Navarro at No. 7 and has demonstrated the ability to step up late in big tournaments in 2024. The Italian won a WTA 1000 event in Dubai earlier this year and reached the final at the French Open, while Navarro will be playing her first career Grand Slam quarterfinal and is 0-1 in WTA 1000 quarterfinals. Paolini got lucky in the Round of 16, as Madison Keys was leading her 5-2 in the third set when Keys got injured and subsequently retired at 5-5, but that near-loss should allow Paolini to swing freely as she looks to improve on her 24-7 record since the start of Dubai. Navarro has knocked off two big names in Naomi Osaka and Coco Gauff, but those wins look a little less impressive when you consider that neither Gauff nor Osaka has reached a Wimbledon quarterfinal.
